Toby Keith’s 1993 debut single, “Should’ve Been a Cowboy,” helped ignite a career that has seen the Oklahoma native win multiple CMA Awards and ACM Awards, earn 20 No. 1 singles and sell more than 40 million albums worldwide.
To celebrate the 25th anniversary of Toby’s breakthrough song and self-titled debut album—which also included Top 5 hits “He Ain’t Worth Missing,” “A Little Less Talk and a Lot More Action” and “Wish I Didn’t Know Now”—Toby’s family, friends and industry insiders gathered at Nashville’s BMI headquarters on Dec. 5 to present Toby with a special citation of achievement.
NFL Hall of Fame member Terry Bradshaw, producer/executive Harold Shedd, and Toby’s daughters Shelley and Krystal and wife Trisha were on hand for the celebration that recognized Toby for more than 7 million broadcast performances of “Should’ve Been a Cowboy.”
Check out some of the photos below, courtesy of Tammie Arroyo, AFF-USA.com.

Toby will perform two shows at the Grand Ole Opry in the Ryman Auditorium on Dec. 7. The following night, he will also perform at the Nashville Symphony’s 34th Annual Symphony Ball where he will be honored with their 2018 Harmony Award, which recognizes an individual who exemplifies the harmonious spirit of Nashville’s musical community.